Functional Groups 2

Question 1

Synthesis of Dienes

Answer 1

1. ) dehydration of diols
2. ) dehydrogenation of alkenes
3. ) dehydrohalogenation of dihalides

Question 2

Dehydration of diols

Answer 2

HOCH2CH2CH2CH2OH

-H2SO4-> CH2=CH-CH=CH2

Question 3

Dehydrohalogenation of dihalides

Answer 3

CH3CHXCH2CH2X
-strong base/heat->
CH2=CH-CH=CH2

Question 4

Reaction of dienes

Answer 4

1. ) addition of hydrogen

2. ) Diels-Alder reaction

Question 5

Preparation of alkyl halides

Answer 5

1. ) alcohol + HX
2. ) alcohol + PX3
3. ) addition of HX to alkenes
4. ) halogenation of alkanes with Cl2 or Br2

Question 6

Reactions of alkyl halides

Answer 6

1. ) synthesis oh higher alkanes
2. ) synthesis of R-OH using NaOH
3. ) elimination
4. ) synthesis of Grignard reagents

Question 7

Formaldehyde (H2C=O) + GR (react with H2O in 2nd step)

Answer 7

Primary alcohol

Question 8

Aldehyde + GR (react with H2O in 2nd step)

Answer 8

Secondary alcohol

Question 9

Ketone + GR (react with H2O in 2nd step)

Answer 9

Tertiary alcohol

Question 10

Nitrile + GR (react with H2O in 2nd step)

Answer 10

Ketone

Question 11

Cabon Dioxide + GR (react with HCl in 2nd step)

Answer 11

Carboxylic acid

Question 12

When to ad -ok to an alcohol

Answer 12

When alcohols have double and triple C-C bonds, add -ok to the end to specify and alcohol; lowest carbon number goes to carbon with -OH

Question 13

Synthesis of alcohols

Answer 13

1. ) Hydration of Alkenes
2. ) hydrolysis of alkyl halides
3. ) preparation from Grignard reagents
4. ) oxymercuration-demercuration of Alkenes
5. ) hydroboration-oxidation of Alkenes

Question 14

Oxidation of primary alcohols to carboxylic acids

Answer 14

RCH2OH -Na2Cr2O7,H2SO4-> RCOOH

Question 15

Oxidation of primary alcohols to aldehydes

Answer 15

RCH2OH -CrO3,PCC-> RCHO

Question 16

Oxidation of secondary alcohols to ketones

Answer 16

R-CH(OH)-R’ -Na2Cr2O7,H2SO4-> R-CO-R’

Question 17

Reduction of alcohols to alkanes

Answer 17

ROH -LiAlH4,TiCl4-> R-H

Question 18

Synthesis of alkyl halides

Answer 18

ROH + HX -> RX

Question 19

Dehydration of Alkenes

Answer 19

CH3CH2OH -acid,heat-> H2C=CH2 + H2O

Question 20

Dehydration to ethers

Answer 20

2ROH + acid ->R-O-R + H2O

Question 21

Tosylation

Answer 21

ROH + tosyl chloride -pyridine(PCC)-> alkyl tosylate

Question 22

Acylation

Answer 22

ROH + ClCOR’ (acyl chloride) -> OR-COR’ (ester)

Question 23

Deprotonation to alkoxide

Answer 23

R-OH + Na -> R-O^- Na^+
Or
R-OH + K -> R-O^- K^+

Question 24

Thiols

Answer 24

Have -SH groups

Question 25

Thiol from alkyl halides and HS-

Answer 25

RX + HS- -> X- + RSH

Question 26

Thiols from disulfides

Answer 26

R-S-S-R (+ Li and liquid NH3) -> RSH

Question 27

Thiols from Alkenes

Answer 27

R’CH=CH2 + H2S (+ RO-) -> RSH

Question 28

Synthesis of thioesters

Answer 28

RSH + R’-COCl -> R’-COSR

Question 29

Synthesis of thioethers

Answer 29

RSH + OH- + R’X -> R-S-R’

Question 30

Synthesis of thioacetals

Answer 30

2RSH + R’-CH=O -> R’-CH(SR2)

Question 31

Synthesis of Sulfonic acids

Answer 31

RSH + KMnO4 -> R-SO3H